Build to Bond: Interview with Grant Halloran, CEO of Planful

I recently went one on one with Grant Halloran, CEO of Planful.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

Grant: I’ve always been intrigued by how business works. As a kid, I started a carwash and lawn service and ‘employed’ half a dozen other kids — my first entrepreneurial venture. My interest in business led me to get a commerce degree at university, where I studied economics, accounting and marketing. I began my career in banking and learned a lot from lending money to entrepreneurs. 

My entrepreneurial experiences as a child inspired me to co-found a company with my brother, Brett, in my 20s. I was fascinated with where technology was headed. I’d read a book called “Being Digital,” by MIT’s Nicholas Negoponte in 1997 and I realized that so much of our analogue life was going to become digitized. During our first business venture, a lot of people told us what we were doing wouldn’t work and that we were going to fail, but we kept our faith in where we believed the world was heading.

We did nearly go broke a few times during our first year. Our parents even took out a second mortgage on their house to help us out, and we borrowed money where we could. We wouldn’t give up. Then something tipped, and we started winning big clients. That experience taught me a lot about perseverance and helped me develop confidence needed to be the business leader I am today. I learned how important it is to have good talent around you and how to develop a strategy.

We did well as our client base grew, but we were defined as an Australian tech business, which was pretty rare back then. So, in 2006, we took the company global. The way we saw it, there was no reason we couldn’t play at the global level like larger international companies.

I’ve found that if you’re sensible and you believe in yourself, you can find success. It’s easier not to take the risk, but calculated risk-taking is how you learn and grow. I learned this from skeptics early on: never let mediocre people bring you down — do your research, believe your gut and trust in your vision. Above all, persevere through roadblocks.

Adam: In your experience, what are the key steps to growing and scaling your business?

Grant: It’s all about solving problems and brainstorming ways to seize an opportunity through first principles, an ancient philosophy used by many successful leaders, including (I’m guessing) Elon Musk. First principles essentially means to remove any preconceived notions or assumptions, and starting from scratch. Copying everyone else or reading a book isn’t enough — I recommend getting out a whiteboard and brainstorming the old-fashioned way. One needs to be imaginative but also try to be bold. Ordinary ideas don’t usually have much impact.

So much of success is about timing. You have to find your opportunity and your product opportunity at the right time. Some people call it luck, but it’s not unusual to get the timing wrong at first, so you have to keep trying, and that’s how you make your own luck.

Another thing that’s absolutely essential to grow and scale successfully is a great team. The people around you are critical, not only in terms of skills and talent stack but also personality. They need to be persistent and have a bias for action. If the people around you don’t have those attributes, it’s really difficult to do smart things quickly.

It’s important to realize that relationships are the foundation of business, so having productive, healthy relationships with your people is critically important. You need a team that you want to go into battle with, people you want to spend time with. At Planful, relationships are the very foundation of our success. As a young entrepreneur, I didn’t realize how important relationships are, so that was a lesson I learned over the years.

Adam: What do you believe are the defining qualities of an effective leader?

Grant: I believe good leaders are open and honest with employees. And I also believe character, empathy and resolve are essential qualities in an effective leader. Whether you lead a small team or an enormous global company, it’s important to connect with employees and make sure they’re okay, especially during a challenging time like a global pandemic. Regular contact also gives you the opportunity to find out what’s happening in your workgroup and learn about new ideas for making the company and team more effective.

People shouldn’t expect perfection from leaders. They won’t always have a solution right away for every problem. But effective leaders are willing to show vulnerability and ask for help. When they don’t know how to address a challenge, they’re not afraid to admit it. And having a leader who is transparent and empathetic brings out the best in the team, inspiring people to come up with new ideas on how to solve a problem.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

Grant: Adversity is one way to hone leadership skills, and we’ve had plenty of that lately with the pandemic. In response, we’ve seen amazing innovation and creativity, which can help leaders take their careers and teams to a new level. We saw a lot of creativity in 2020 and into this year when we all had to adjust to new ways of working. Some observers speculate that the public health situation curtailed innovation, but I think it directed it inward, with individual leaders and teams finding new ways of working and serving customers.

People are finding new ways to connect and collaborate. They’re discovering new ways to strengthen their company culture despite the lack of in-person contact. I think when the pandemic is under control and things return to whatever the new version of normal is, we’ll have enough space and perspective to realize how incredibly adaptive we are. We’ll recognize that so many people stepped up and ensured business continuity and made sure customers got the service and support they need under difficult circumstances.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

Grant: This first tip was always true, but it might resonate even more today because of the uncertain business climate: Learn to be comfortable with uncertainty. Whether you’re an entrepreneur, an executive or a civic leader, you’ve got to make peace with uncertainty because change is happening all the time, and if you keep your organization agile and responsive, you’ll be able to take advantage of new opportunities and mitigate risk by reacting quickly when business conditions evolve.

Secondly, I’d advise people to constantly evaluate practices and processes that are in place in their organization and make sure they still work. “We’ve always done it this way” isn’t a good reason to continue doing things a certain way. There is almost always a way to improve anything and there is usually a lot of slack in any business that can be harnessed.  Personally, I like to push people close to their limits, and I don’t apologize for that. Those who’ve worked with me a long time have seen how that has helped them grow faster in their career.

Thirdly, focus on connecting with people and collaborating across your organization. A business is a big interconnected web of activities so effective leaders drive their teams to collaborate across the whole company, rather than staying in their department silos. 

Adam: What is your best advice on building, leading and managing teams?

Grant: Build a team that is able to bond. Depending on the size of the company, there can be a lot of people involved in recruiting, so it’s important to have objective criteria for evaluating candidates. One thing to keep in mind is that statistically speaking, what people have done in the past is a good indicator of what they’ll do in the future.

Be ok with mistakes. But the caveat to that is this: a servant leader doesn’t disengage and let their people make mistakes that are large or irreparably damage the company, or that person’s career.

Earlier we talked about people with a bias for action being essential to an effective team. When building a team, keep traits that are important to you in mind and document what a candidate for a job has done that demonstrates those traits. Look for examples in their history when they were dedicated to a task and got it done despite difficulties. Look for clarity and the ability to take ownership and responsibility.

Adam: What are your best tips on the topics of sales, marketing and branding?

Grant: For sales, I think the best approach is to flip the “sales cycle” script and think of the buyer’s cycle instead. You’re walking potential buyers through a journey, and it’s your job to smooth the way and act as a steward. Think of your role as the person who helps the buyer on their journey, not just as a person who is there to sell them something. Get excited about having a solution to their problem.

Marketing success requires an understanding of the psychology of persuasion on a fundamental level. You are trying to change people’s minds. The best marketers understand that and keep that goal front and center, taking persuasion into account in every interaction. They also know quality matters and that if you put garbage into the machine, you’ll get garbage out.

Branding is all about creating an overall sense of who your company is, and the ultimate objective is to get it down to one word that people associate with you, the way “Disney” instantly conjures up images of “family.” Every interaction someone has with your brand — your website, your ads, your whitepapers — it all contributes to building your brand. Everyone in your company is a brand ambassador too. Anytime you talk to someone on the phone, send an email, have a brief chat on an elevator, go to a barbeque — you’re a brand ambassador in every one of those interactions.

Adam: What is the single best piece of advice you have ever received?

Grant: The best piece of advice I’ve ever received is that leadership is situational, and you can’t project the same leadership style all the time. You have to be adaptable to fit the circumstances. Sometimes you have to be dramatic to effect change. Sometimes you need to be consultative. Sometimes you’re a general directing troops. The point is there’s not one model for leadership; you have to be a chameleon.

The initial phases of the COVID-19 crisis required a directive approach. There wasn’t a lot of time for consultation because the situation required direct and speedy action, and people needed to know what the plan was so they could execute on it. Later, it was possible to step back and be empathetic, checking in to make sure everyone is doing well. Different situations call for different leadership styles. 


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

Follow Adam on Instagram and Twitter at @adammendler and listen and subscribe to Thirty Minute Mentors on your favorite podcasting app.